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Vacation rentals in Gualdo

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Top-rated vacation rentals in Gualdo

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
Villa in Castelraimondo
4.82 out of 5 average rating, 11 reviews

Villa Ermelinda · Ville Carborello Weddings

Villa Ermelinda is a private 16th-century villa set among the rolling hills of Le Marche, ideal for intimate weddings, destination weddings and exclusive stays. It offers exclusive use, a panoramic pool, gardens, a big terrace and beautiful spaces for symbolic ceremonies, poolside aperitifs and dinners under the stars. Hosting up to 18 guests, it also works perfectly with nearby Villa Nasca & Villa Adele, just a few minutes away, for larger wedding groups and unforgettable wedding weekends.

Guest favorite
A serene swimming pool is situated on a deck, featuring clear turquoise water under a bright sky. An umbrella provides shade beside chaise lounges. Scenic hills and mountains stretch into the distance, creating a picturesque backdrop of nature.
Home in Penna San Giovanni
5.0 out of 5 average rating, 8 reviews

GrazieSole Agriturismo exclusive whole house

The GrazieSole farmhouse is a newly renovated 1900s farmhouse, in a characteristic style with original stone walls, exposed bricks and ceilings with wooden beams, it has a 12-metre swimming pool with breathtaking views and a wide panorama that extends from the Sibillini Mountains to the adjacent hillside villages. It is located in open countryside one kilometer from the center of the village of Penna S. Giovanni, in a sunny and quiet position, surrounded by a garden and large green spaces.

Villa in Gualdo
5.0 out of 5 average rating, 3 reviews

La casa di Iole

Distesa su una collina ,la nostra casa vacanze offre una vista mozzafiato dei monti sibillini. Il giardino e la piscina sono pensati per il relax ed il divertimento dei più piccoli. Per gli amanti dell’avventura, il Parco Nazionale dei Monti Sibillini offre sentieri per trekking e mountain bike, mentre in 20 minuti raggiungerete il Lago di Fiastra. Se amate il mare, le spiaggie sono raggiungibili in 45 minuti in una strada panoramica tra le colline. A solo un'ora circa da Assisi e Perugia.

Guest favorite
An open living area features a gray sofa adorned with cushions, paired with a simple black dining table set for two. A compact kitchen with white cabinetry and a black countertop sits in the corner, while light flows in through windows framed by exposed brick walls.
Apartment in Sarnano
4.86 out of 5 average rating, 80 reviews

In the heart of the village apartments

Take a break from the hustle and bustle of everyday life. Come and relax within the walls of the beautiful medieval center of Sarnano. Right along the staircase that leads to the main square of the town, there is this new apartment with kitchen and living room, bedroom with 2 single beds or 1 double bed and sofa bed, bathroom equipped with shower. Magnificent view of the Sibillini mountains. Great starting point for walks. Possibility to store motorcycles and recharge e-bikes nearby.

Guest favorite
The image captures a scenic view of La Roccaccia, featuring a private pool and lush greenery. Stone pathways meander through the garden, with tall cypress trees framing the scene, while a historic tower is visible in the background against a clear blue sky.
Castle in Montefortino
5.0 out of 5 average rating, 7 reviews

MarcheAmore - La Roccaccia, La Sibilla Apartment

La Roccaccia was built in 1080 AD as a lookout tower to defend the Fermo area. Located in an enchanting setting between Monte Sibilla, the gorge of Infernaccio and the hilltop town of Montefortino. Today La Roccaccia is a luxury venue with private pool and jacuzzi located among the Sibillini mountains, designed for those in search of peace, relaxation and meditation. Its park is filled with works of art and at it features a private amphitheater with a unique view.

An aerial view showcases the villa surrounded by greenery, highlighting the private pool and shaded seating areas. The building features a traditional stone exterior with a tiled roof, set against a backdrop of rolling hills and diverse vegetation.
Home in Gualdo
4.94 out of 5 average rating, 16 reviews

Casa Santo Stefano, panoramic view, swimmingpool

Casa Santo Stefano is a unique location if you want to relax. The villa is located at the foot of the world-famous Sibillini Mountains at 650m altitude. On private grounds of more than 10,000m2, you will find yourself in an oasis of peace and enjoy the breathtaking rolling valley and the Sibillini Mountains. You can choose to do nothing at all and drink an espresso at the private pool, but if you want a more active vacation, there are plenty of options. Be welcome!

Superhost
An indoor wellness area features a heated hydromassage minipool for six, surrounded by wide glass panels that provide views of the lush outdoor landscape and an inviting blue swimming pool beyond. Natural wood beams enhance the room's warm aesthetic.
Apartment in Gualdo
5.0 out of 5 average rating, 7 reviews

Agriturismo Elisei – attic, pool, sauna, spa

Are you looking for a quiet, relaxing place, surrounded by nature and away from the hustle and bustle? Do you want to discover the charm of the Monti Sibillini National Park and its villages? Choose the Elisei Farmhouse, small and for a few people, allowing each of the guests to have plenty of outdoor space. The farmhouse has a large garden with swimming pool, as well as a wellness area with sauna and spa. CIN (National Identification Code): IT043021B5CETGSYCI

Villa in Montefortino (FM)
4.6 out of 5 average rating, 5 reviews

VILLA SERRA - Sibillini Retreat

COMPLETELY RENOVATED - NEW OPENING 2026 Villa Serra Sibillini Retreat is a detached property with a large garden overlooking the Sibilla and Vettore mountains. The property has three double bedrooms with high-quality king-size Reactive mattresses, one of which has twin beds that can be separated upon request. It now offers spa services, a Finnish sauna overlooking the Sibilla, and a heated whirlpool tub, included with your reservation year-round.

Superhost
Apartment in Sarnano
4.89 out of 5 average rating, 9 reviews

Historic frescoed residence and Sibillini Mountains view

Discover the charm of Sarnano, one of the most beautiful villages in Italy. In this cozy retreat in the heart of the historic center, halfway up the suggestive staircase that leads to Piazza Alta, you will experience an authentic stay among art, history and relaxation. With 2 bedrooms, 1 bathroom and a bright living area with a kitchen, the house offers a splendid view of the Sibillini Mountains that will make your vacation truly unforgettable.

Top guest favorite
A charming, two-story farmhouse features terracotta walls and a sloped roof, surrounded by lush greenery. Potted plants frame the entrance, with a wooden table and chairs positioned outside under a shaded umbrella, offering inviting outdoor seating and scenic countryside views.
Villa in Sant'Angelo in Pontano
4.98 out of 5 average rating, 41 reviews

Traditional 3-bedroom cottage with large garden

Forget your worries in this spacious and serene space. Absolutely tranquil, but less than a five minute drive from the bustling village of Sant’Angelo, which has three restaurants, three bars, and a theatre, as well as all local services. Relax and enjoy the views in the garden, or drive half an hour to the beach or a lake in the mountains, or explore the many beautiful hilltop towns in the area. Something for all tastes!

Superhost
Villa in Sant'Angelo in Pontano
5.0 out of 5 average rating, 5 reviews

Villa in the Sibillini Mountains, Pool & Privacy

Private pool villa in Sant’Angelo in Pontano, among the rolling hills of Marche at the foot of the Sibillini Mountains. Sleeps up to 8 with 4 double bedrooms, all with en-suite bathrooms (3 upstairs + 1 in a separate annex), Wi-Fi and air conditioning. Large shaded porch for outdoor dining, lounge corners, and an outdoor BBQ/oven area. Great base for the Sibillini Park and Lake Fiastra.

Top guest favorite
A wooden cabin is surrounded by lush greenery and wildflowers, showcasing a welcoming entrance and large windows. The sunlight highlights the natural colors of the exterior, creating a serene atmosphere in harmony with the surrounding landscape.
Tiny home in Sarnano
5.0 out of 5 average rating, 21 reviews

Montequieto: peace and nature by the Sibillini.

Located just outside Sarnano, Montequieto is a wooden cottage nestled in nature, with breathtaking views of the Sibillini Mountains. Ideal for relaxing, exploring the surrounding trails, venturing into the unspoiled landscapes of the Monti Sibillini National Park or discovering the medieval village of Sarnano, one of the most beautiful in Italy.

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